The Bangles, 1988

Never a band that took to blending in—as evidenced by the videos for their '80s punk-rock anthems like "Walk Like an Egyptian" and "Manic Monday"—The Bangles rocked a level of hair color, texture, and style variety not seen again until The Spice Girls.

Drew Barrymore, 1995

So many iconic things happening here, where do we even start? Obviously, there's the Marilyn wig. (Wig, right? That's got to be.) And then the brows! Who didn't pluck theirs into oblivion because of Drew? And could this perhaps be the inspiration for her makeup line, Flower?

Jennifer Love Hewitt, 1998

Twisted in the front, ringlets in the back: This is the look that launched a million prom hairstyles. (P.S.: For all the JLH stans in the house, you'll remember this is the year she brought Carson Daly as her date. Memories.)

Renee Zellweger, 1999

Renee is an incredibly strong and confident woman (just check out the powerful essay she recently wrote), so we're not surprised she was able to move past this look. But to be fair, we're sure you probably ran straight to your crimper the next morning to copy this.

Macy Gray, 2000

Macy Gray's hit single "I Try" will go down in history as stuck in our heads and this monochromatic look—complete with deep magenta afro—will go down in our hearts as one of the rare natural hair red carpet moments in the early 2000's.